GB2055117A - Improvement in or relating to organic compounds - Google Patents
Improvement in or relating to organic compounds Download PDFInfo
- Publication number
- GB2055117A GB2055117A GB8022203A GB8022203A GB2055117A GB 2055117 A GB2055117 A GB 2055117A GB 8022203 A GB8022203 A GB 8022203A GB 8022203 A GB8022203 A GB 8022203A GB 2055117 A GB2055117 A GB 2055117A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- compound
- compounds
- parts
- dyeing
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000002894 organic compounds Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- 239000000203 mixture Chemical group 0.000 claims abstract description 14
- 239000002253 acid Substances 0.000 claims abstract description 8
- 150000003839 salts Chemical group 0.000 claims abstract description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 15
- 238000004043 dyeing Methods 0.000 claims description 14
- 239000000975 dye Substances 0.000 claims description 12
- 239000000758 substrate Substances 0.000 claims description 7
- 239000004952 Polyamide Substances 0.000 claims description 6
- 125000000129 anionic group Chemical group 0.000 claims description 6
- 229920002647 polyamide Polymers 0.000 claims description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000010985 leather Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229920000098 polyolefin Polymers 0.000 claims description 2
- 229920002635 polyurethane Polymers 0.000 claims description 2
- 239000004814 polyurethane Substances 0.000 claims description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 6
- 150000001768 cations Chemical class 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 210000002268 wool Anatomy 0.000 description 4
- 239000004677 Nylon Substances 0.000 description 3
- 238000006266 etherification reaction Methods 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- -1 sulpho group Chemical group 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical class [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 159000000000 sodium salts Chemical group 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- ADVGKWPZRIDURE-UHFFFAOYSA-N 2'-Hydroxyacetanilide Chemical compound CC(=O)NC1=CC=CC=C1O ADVGKWPZRIDURE-UHFFFAOYSA-N 0.000 description 1
- 229920000161 Locust bean gum Polymers 0.000 description 1
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- NGPGDYLVALNKEG-UHFFFAOYSA-N azanium;azane;2,3,4-trihydroxy-4-oxobutanoate Chemical compound [NH4+].[NH4+].[O-]C(=O)C(O)C(O)C([O-])=O NGPGDYLVALNKEG-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010016 exhaust dyeing Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 235000010420 locust bean gum Nutrition 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 238000009980 pad dyeing Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000009977 space dyeing Methods 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/08—Disazo dyes from a coupling component "C" containing directive hydroxyl and amino groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/28—Preparation of azo dyes from other azo compounds by etherification of hydroxyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
The present invention relates to compounds of formula I, <IMAGE> in which R is ethyl or ethyl, and mixtures of such compounds, which compounds are in free acid or salt form and are useful as dyestuffs.
Description
SPECIFICATION
Improvements in or relating to organic compounds
The present invention relates to anionic disazo compounds, their preparation and use as anionic dye-stuffs.
More particularly, the present invention provides compounds of formula I,
HO3 S v N=NM-QN=NQ OR in which R is methyl or ethyl, HOOCH3 and mixtures of such compounds, which compounds are in free acid or salt form.
The present invention further provides a process for the production of compounds of formula land mixtures thereof, comprising etherifying a compound of formula II
The etherification may be effected in known manner. Preferably, the etherification is carried out employing the corresponding dialkylsuphate. The reaction is suitably carried out in aqueous alkaline medium, the preferred pH being from 9 to 11. The reaction temperature is suitably from 30 to 90"C, more preferably from 40 to 70"C.
The compounds of formula I obtained may be isolated in accordance with conventional methods. It will be appreciated that, depending on the reaction and isolation conditions, the compounds of formula I may be obtained in salt form, which compounds may be converted into free acid form by known methods. The neutralizing cation of the sulpho group is not critical and may be any one of those non-chromophoric cations conventional for the salt form of anionic dyestuffs. Examples of such cations are alkalimetal cations and cations of the ammonium type e.g. lithium, sodium, potassium, ammonium, mono-, di-, tri- and tetra-methylammonium, triethylammonium, mono-, di-and triethanolammonium. The preferred cations are lithium, sodium and potassium, with sodium being the most preferred.
The compounds of formula II may be prepared by coupling the diazonium derivative of the compound of formula III,
in alkaline medium with a compound of formula IV
Diazotization to produce the starting material and the coupling reaction may be effected in accordance with known methods. The starting materials of formulae Ill and IV are known.
The compounds of formula I, and mixtures thereof are useful for dyeing or printing anionic dyeable substrates. Suitable substrates include leather, natural and synthetic polyamides, polyurethanes or basic-modified polyolefins. Especially suitable are textile substrates consisting of or comprising natural and synthetic polyamides, such as wool and silk, and particularly nylon. The dyestuffs may advantageously be used for carpet printing.
Dyeing and printing may be carried out in accordance with known methods, for example pad dyeing or exhaust dyeing, especially the latter as the compounds of formula I and mixtures thereof build-up from a neutral dye bath.
Furthermore, the compounds of formula I and mixtures thereof are also useful for use in the "space-dyeing" process.
The compounds of formula I, and mixtures thereof, may be employed as such or may be used in the form of liquid or solid preparations. The preparation of stable liquid, for example concentrated aqueous preparations, or solid preparations may be carried out in accordance with conventional methods, for example by dissolving in suitable solvents, optionally with the addition of conventional additives such as solubilizing agents, for example urea, or by grinding or granulating. Such preparations may be obtained in accordance with the procedure described in French Patents 1,572,030 and 1,581,900.
Further, the compounds of formula I, and mixtures thereof, may be made up into preparations which are dispersible in cold water. Such dispersions may be prepared, for example, by grinding the dye wet or dry in the presence of one or more conventional anionic dispersing agents and optionally in the presence of other conventional additives, with subsequent spray-drying. The preparations so obtained are finely dispersed in cold water.
The compounds of formula I, and mixtures thereof are well soluble in water, build-up well, migrate well and give even dyeings, especially on stripy nylon. The dyeings obtained possess notable light-fastness.
Furthermore, the compounds of formula I and their mixtures give dyeings which have notable general fastnesses, such as wet-fastnesses, especially wash-, water-, milling- and sweat-fastness.
The compounds of formula I are suitable for combining with other dyes having neutral build-up, whereby tone-in-tone dyeings having the above-mentioned advantageous properties are obtained. Further, such dyeings do not exhibit catalytic fading.
The following Examples further serve to illustrate the invention. In the Examples, all parts are by weight and all degrees are in degrees Centigrade.
Example 1
27.7 Parts of 4-amino-1,1 '-azobenzene-4'-sulphonic acid are dissolved at 60 in 300 parts water at pH 9-10 by the addition of a 30% sodium hydroxide solution and are then mixed with 6.9 parts sodium nitrite dissolved in 25 parts water. The nitrite containing aminoazo dyestuff solution is added dropwise, over a period of 15 minutes, to a reaction vessel containing 35 parts 30% hydrochloric acid, 50 parts water and 150 parts ice, the reaction temperature being 0-5". After stirring for 1 hour the excess of sodium nitrite is destroyed by adding amido-sulphonic acid.
15.4 Parts 1-acetylamino-2-hydroxybenzene are dissolved in 120 parts water and 10 parts 30% sodium hydroxide solution. The diazonium solution obtained as described above is added dropwise thereto over the period of 30 minutes, the pH of the solution being maintained at 10 by the addition of 30% sodium hydroxide solution. After a further 1 hour stirring, the pH is adjusted to 7.5-8.0. The precipitated dyestuff is isolated by filtration and washed with 5% sodium chloride solution.
The obtained filtercake is dissolved at 40 in 600 parts water by adding 10 parts 30% sodium hydroxide solution and is then mixed with 63 parts dimethylsulphate over the period of 30 minutes. During the 30 minutes the pH is maintained at 10.5-11.0 by the dropwise addition of 55 parts 30% sodium hydroxide solution and the temperature is held at 400, after which the etherification is complete. Isolation of the precipitated dyestuff is effected by filtration followed by washing with 2.5% aqueous sodium chloride solution and drying.The dyestuff which, in the free acid form, corresponds to the formula
is obtained in the sodium salt form; it is a red powder which gives an orange colour when dissolved in water and gives dyeings on wool and synthetic polyamides of clear reddish-yellow shades which have good light-and wet-fastnesses.
Example 2
In analogy with the procedure described in Example 1 employing the correspoding amount of diethylsulphate (82 parts) instead of 63 parts dimethylsulphate, the dyestuff which, in the free acid form, corresponds to the formula
is obtained in the sodium sa It form and gives dyeings on wool and synthetic polyamides of reddish-yellow
shades having good light- and wet-fastnesses.
The dyestuffs of Examples 1 and 2 which are in the sodium salt form, may, depending on the reaction and
isolation conditions, be obtained in free acid form or in other salt forms, for example those salt forms
indicated in the description hereinbefore.
Application Example A:
100 Parts of pre-wetted synthetic polyamide, for example nylon 66, are entered at 40 into a dyebath
consisting of 4000 parts of water, 10 parts of anhydrous sodium sulphate and 2 parts of the dyestuff from Example 1 or2.
The dye I liquor is heated over the course of 30 minutes to boiling temperature and kept at this temperature
for 1 hour. 4 Parts of glacial acetic acid are then added thereto and dyeing is completed with heating for a
further 30 minutes at boiling temperature. During dyeing, the water that evaporates is continuously
replaced. The reddish-yellow dyed nylon cloth (for both dyestuffs) is then removed from the liquor, rinsed
with water and dried. Wool may also be dyed by the same process.
The dyeings have notable wet- and light-fastnesses.
Application Example B:
Polymide is printed with a printing paste containing:
30 parts dyestuff of Example 1 or 2
50 parts urea
50 parts solubilizing agent (e.g. thiodiethylene glycol)
290 parts water
500 parts suitable thickening agent (e.g. based on carob bean gum)
20 parts acid donating agent (e.g. ammonium tartrate)
60 partsthiourea.
The printed textile goods are steamed for 40 minutes at 1020 (saturated steam), rinsed cold, subsequently washed at 60 for 5 minutes with a dilute solution of a conventional detergent and rinsed again with cold water. A reddish-yellow print having notable light- and wet-fastnesses is obtained with each of the two dyestuffs.
Claims (9)
1. A compound of formula I,
in which R is methyl or ethyl, and mixtures of such compounds, which compounds are in free acid or salt form.
2. A lithium, sodium or potassium salt of a compound according to Claim 1.
3. A process for the production of a compound of formula I, or a mixture thereof, as defined in Claim 1, comprising etherifying a compound of formula 11
4. A process for the production of a compound of formula I, or a mixture thereof, as defined in Claim 1, substantially as hereinbefore described with reference to Example 1 or 2.
5. A compound of formula I, whenever obtained by a process according to Claim 3 or Claim 4.
6. A process for dyeing or printing anionic dyeable substrates, comprising employing a compound or mixture according to Claim 1 or Claim 5, as dyeing agent.
7. A process according to Claim 6, in which the substrate consists of or comprises leather, natural or synthetic polyamides, polyurethanes or basic-modified polyolefins.
8. A process for dyeing or printing anionic dyeable substrates, substantially as hereinbefore described with reference to Application Example A or B.
9. Dyed or printed substrates, whenever obtained by a process according to any one of Claims 6 to 8.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH647879A CH642096A5 (en) | 1979-07-11 | 1979-07-11 | ANIONIC DISAZO CONNECTIONS AND THEIR PRODUCTION. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2055117A true GB2055117A (en) | 1981-02-25 |
| GB2055117B GB2055117B (en) | 1983-04-07 |
Family
ID=4310288
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8022203A Expired GB2055117B (en) | 1979-07-11 | 1980-07-07 | Organic compounds |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5616558A (en) |
| CH (1) | CH642096A5 (en) |
| DE (1) | DE3022928A1 (en) |
| FR (1) | FR2460978A1 (en) |
| GB (1) | GB2055117B (en) |
| IT (1) | IT8049217A0 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6022893U (en) * | 1983-07-23 | 1985-02-16 | 株式会社村田製作所 | Shield structure of circuit board equipment |
| JPS63121494U (en) * | 1987-01-30 | 1988-08-05 | ||
| US5053924A (en) * | 1990-03-30 | 1991-10-01 | Motorola, Inc. | Electromagnetic shield for electrical circuit |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH628667A5 (en) * | 1977-03-14 | 1982-03-15 | Sandoz Ag | Process for preparing anionic disazo compounds |
-
1979
- 1979-07-11 CH CH647879A patent/CH642096A5/en not_active IP Right Cessation
-
1980
- 1980-06-19 DE DE19803022928 patent/DE3022928A1/en not_active Withdrawn
- 1980-07-07 GB GB8022203A patent/GB2055117B/en not_active Expired
- 1980-07-10 JP JP9337980A patent/JPS5616558A/en active Pending
- 1980-07-11 FR FR8015488A patent/FR2460978A1/en active Granted
- 1980-07-11 IT IT8049217A patent/IT8049217A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2460978A1 (en) | 1981-01-30 |
| JPS5616558A (en) | 1981-02-17 |
| FR2460978B1 (en) | 1984-09-28 |
| GB2055117B (en) | 1983-04-07 |
| CH642096A5 (en) | 1984-03-30 |
| IT8049217A0 (en) | 1980-07-11 |
| DE3022928A1 (en) | 1981-01-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |